A divergent synthesis of 1-aminonaphthalenes by the Diels-Alder reaction of 3-aminoarynes followed by diversification is disclosed. The cycloaddition of 3-aminoarynes with 2-substituted furans exhibits unusual proximal selectivity. Owing to the significant versatility of the resulting tricyclic ethers, a wide variety of highly functionalized 1-aminonaphthalenes can be prepared, thereby enabling rapid development of fluorescent dyes.
Okada et al. (Fri,) studied this question.